Cleveland mentors Kenny (Kanye West) to help get his rap career off the ground.

When Cleveland and Donna attempt to celebrate their anniversary, their unruly kids and disruptive friends, including Donna's ex-husband, Robert, get in their way

After his confidence is shattered, Cleveland vows to find his mojo again, and decides that a family vacation to Africa will do the trick. While on a layover in Hawaii en route, Cleveland gets derailed by mai tais, the ocean and plenty of sunshine, and realizes a few days in paradise is actually what he needs.

Cleveland crushes Cleveland Jr.'s spirit when he forbids him from trick-or-treating because he thinks he is too old.
Junior reinvents himself as a "cool kid" and is invited to attend a Halloween party with Roberta.
When he gets picked on and is unhappy with his new persona, Cleveland and the gang come to Junior's rescue and encourage his enthusiasm for the holiday.

Coach Cleveland gets greedy to win the high school baseball state championship game and turns to cheating when his star pitcher goes out for the season.

Cleveland Jr. and Kendra, ashamed of their appearance in a swimsuit, feel left out of the fun when the family spends an afternoon in the pool and petition to pass a bill to grant equal rights for those who are overweight.

Donna's show-off and bossy sister, Janet, and her unruly children come to town to celebrate Thanksgiving with the Browns. Cleveland, still bruised by their past, wants nothing to do with her this Thanksgiving and attempts to drive her out.

When Rallo's teacher forces him to spend the weekend at a retirement home to get to know the senior citizens during the holidays, he meets Murray, who teaches him about Hanukkah. In an attempt to rekindle Murray's holiday spirit, Rallo helps him escape, but when his new friend's health begins to suffer, Rallo has to bring Murray back to the home.

Donna, frustrated by her husband's laziness on the weekends, nags Cleveland to help her around the house and to do something more with his life. To prove to Donna he can be as charitable as her, Cleveland recruits his buddies from Quahog and Stoolbend to participate in the First Annual Charity Beer Walk.

At Donna's suggestion, Cleveland and Rallo start spending more time together causing Cleveland Jr. to become jealous of their new relationship.

After Cleveland criticizes her parenting skills, Donna lets him deal with Roberta by himself.

When a management position opens up at Waterman Cable, Cleveland and Terry are surprised when Tim gets the job.
At first Cleveland thinks it will be great to have his friend as his boss, but when Tim goes on a power trip and schedules a company retreat during Cleveland's Super Bowl party, Cleveland must take matters into his own hands to put a stop to Tim's tyrannical ways.

Cleveland and Donna celebrate Valentine's Day with a trip to Los Angeles after scoring courtside seats to the all-star basketball game. Caught up in the excitement, Cleveland gets rowdy and talks smack to the players from the sideline throughout the game.
The basketball champs, feeling hurt, seek revenge by paying a surprise visit to Stoolbend and putting Cleveland in his place.

Cleveland discovers a shocking secret about his wife & his best friend Terry.
Meanwhile, Cleveland Jr. tries to get Rallo to break a nasty habit.

After Cleveland fights to save the town's drive-in movie theater, his efforts to preserve the town's history is noticed by the Stoolbend Preservation Society and he is invited to attend a private dinner party at the home of the great-great-grandson of the town's founding father.

When Cleveland sees all of his childhood possessions around town, he learns that his parents, Freight Train and Cookie, have been selling his stuff to get money after being scammed out of their life savings.
Together, Cleveland, Freight Train and their friends get together to bring down the con man who targeted their family.

When Lester invests in Cleveland's beer truck business and loses his life savings, he is so upset that he decides to take his own life - or does he?
Meanwhile, Rallo is tired of getting his hair cut by his mom and opens his own barbershop in the kitchen.

When Cleveland is reunited with his former high school classmate, "Fatty Patty", who is now skinny, beautiful and still has a crush on Cleveland, Donna becomes extremely jealous and wary of Patty's motives for wanting to be friends with Cleveland.

Cleveland and his friends prepare to enter Stoolbend's annual boat race as a team, but when Cleveland's celebrity idol moves to town, Cleveland makes it priority to befriend him.
And when his new pal invites him to join his boating team, Cleveland is forced to make a difficult decision.

When Cleveland Jr. bonds with Donna's ex-husband, Robert, Cleveland becomes jealous that Jr. thinks Robert is so much cooler than him.

When Rallo and his pals Bernard and Theodore perform in the school talent show, their rap about fiscal responsibility is not well-received by their classmates.
Meanwhile, after Cleveland gets his own cable-access television show, the reviews are less than positive so he takes some tips from the most successful daytime talk shows that appeal to women

Cleveland takes the entire family to a comic convention in an attempt to sell his comic book, "Waderman".
While there, Donna is horrified to find out that Robert Rodriguez is screening a Blaxploitation film that she starred in when she was younger.